View All Kenwood Chicago IL Coach House Homes Listings

8 Beds ⋅ 5 Baths ⋅ 12752094 MLS ⋅ NEW Status

Situated on one of the most desirable blocks in the heart of the Kenwood Historic District, this remarkable residence is distinguished by its striking crow-stepped gable and extraordinary architectural detail. Built in 1896, at the height of Chicago's fascination with revival architecture, the home was designed by noted architect William Otis, a graduate of Paris's prestigious Ecole des Beaux-Arts. His design captures the elegance and craftsmanship of 17th-century Dutch architecture, adding to the neighborhood's character. Exceptionally preserved, the house offers a rare combination of architectural authenticity, gracious scale, and thoughtful modern updates. Beyond its richly detailed brick facade, the interior unfolds with abundant natural light and an extraordinary collection of original craftsmanship, including finely carved woodwork, art glass, and decorative tile. Expansive formal living and dining rooms provide an elegant setting for entertaining, while the warm, inviting kitchen flows naturally into a sun-filled family room and out to a spacious deck - creating an effortless connection between formal and everyday living. With eight bedrooms, multiple fireplaces, and a dramatic third-floor family room featuring soaring 15-foot ceilings, the home offers remarkable scale and versatility. Every floor reveals another layer of the house's architectural character and thoughtful design. The beautifully landscaped, tree-lined lot is further enhanced by a charming coach house with a two-bedroom apartment, offering exceptional flexibility for guests, extended family, a private office, or supplemental income. Timeless in character and sophisticated in its proportions, this extraordinary residence represents a rare opportunity to become the steward of one of Kenwood's treasured pieces of architectural heritage-a home where history, craftsmanship, and modern living come together with grace.

4923 S Greenwood Avenue, Chicago

$200,000

2 Beds ⋅ 1 Baths ⋅ 12629042 MLS ⋅ CONTINGENT Status

Unlock the potential of this Hyde Park/South Kenwood coach house-an ideal opportunity for investors ready to bring their vision to life. This 2-bedroom, 1-bath property offers over 1,100 square feet of living space, featuring generously sized closets and abundant natural light throughout. A rare highlight is the expansive 3-car garage, adding significant value and versatility. With solid bones and endless possibilities, this property is perfect for a full renovation project.*****Highest and Best due by Friday, May 1st, 7 pm-no escalation clauses *****

1145 E 50Th Street, Chicago

$2,900,000

7 Beds ⋅ 5 Baths ⋅ 12540892 MLS ⋅ PENDING Status

New on Woodlawn Avenue. Located in the heart of the South Kenwood Historic Landmark District, this imposing and gracious three-story brick residence is a rare architectural offering. Originally designed and constructed in 1904 by noted architect George Beaumont for prominent Chicago industrialist and philanthropist Bernard E. Sunny, the home was thoughtfully and comprehensively updated in 1937 with striking Art Deco era finishes, seamlessly blending historic character with modern livability. The light-filled interior is ideally suited for today's lifestyle, featuring an open and expansive floor plan across all three upper levels. A welcoming entrance opens to a dramatic oval reception hall, anchored by a sweeping curved staircase leading to the second floor. From this impressive entry, gracious rooms flow into a grand living room, formal dining room, designer kitchen with butler's pantry, and a cheerful breakfast room overlooking a private backyard with patio and garden areas. A true standout is the library off the living room, complete with distinctive leather-clad walls and a hidden bar, perfect for entertaining. The second and third floors open on to substantial landings and each features three bedrooms, two full baths, and additional flexible rooms ideal for offices or dens. Each bedroom is generously sized and uniquely detailed, with special features such as a sun porch, private terrace, or semi-enclosed reading nook. Abundant closet space is found throughout the home. The full-height basement provides excellent recreation and work-out space along with ample storage. Adding exceptional value, the rear of the property includes a recently renovated two-story coach house featuring a three-car garage on the main level and a beautifully appointed one-bedroom apartment above, complete with new windows, central air conditioning, in-unit laundry and up-to-date kitchen and bath, ideal for guests, in-law living, a nanny suite, or rental income. Conveniently located near The University of Chicago campus (including the Lab Schools), Lake Shore Drive, Metra stations, and downtown bus routes, this remarkable home offers historic elegance, modern comfort, and outstanding accessibility.

4933 S Woodlawn Avenue, Chicago

$2,050,000

5 Beds ⋅ 6 Baths ⋅ 12541443 MLS ⋅ CLOSED Status

A true rarity in historic Kenwood, this move-in-ready urban estate was meticulously restored during a multi-year renovation, reemerging as a masterful blend of early 20th-century elegance and modern luxury. Set on an expansive 50 x 300-foot lot within the historic district, the 1904 J.B. Cole residence was once praised by The Economist as "a picturesque structure in old English style of architecture"-a distinction it proudly maintains today. Regal stone lions still guard the original ornamental iron doors, opening to a dramatic foyer with a paneled fireplace and built-in seating. A sweeping circular staircase, illuminated by a period chandelier, sets an immediate tone of grandeur. The reimagined main level unites the home's two original parlors into elegant open-concept living and dining spaces, ideal for entertaining. Pocket doors lead to a chef's kitchen featuring stainless steel appliances, quartzite countertops, and generous banquette seating. French doors open to a sunroom and expansive deck overlooking the beautifully landscaped, fully fenced backyard. The second floor is anchored by a luxurious primary suite offering a huge custom walk-in closet, marble spa bath with steam shower, and a sun-filled, heated porch with serene backyard views. Two additional bedrooms, each with decorative fireplaces, share a thoughtfully updated bath. The third level provides two generously sized en-suite bedrooms with custom closets and steam showers. Wide-plank wood floors and custom windows are throughout, while the fully finished lower level lives like a home of its own. Heated with radiant flooring, it includes a spacious family/media room, large laundry room, fifth bedroom with walk-in closet, abundant storage, and a wine cellar tucked beneath the front porch. Completing the property is a Coach House with a four-car garage and a spacious flex space above-ideal for guests, office or gym. Ideally located near the University of Chicago, the Laboratory Schools, and Kenwood's dining, shopping, and cultural amenities, this is more than a home-it's a lifestyle. A rare opportunity to own a meticulously restored piece of Kenwood history, exquisitely reimagined for modern living.

4730 S Greenwood Avenue, Chicago

$987,500

5 Beds ⋅ 5 Baths ⋅ 12453495 MLS ⋅ CLOSED Status

Spacious is the word that comes to mind as you view this solid brick residence in the well sought after Hyde park area. This property has a connection to the 44th president Barack Obama as the family grew up with them & shared a backyard. The 2 1/2 garage was leased to the secret service detail assigned to protect the Obama's. The former garage, now two story coach house, was rehabbed to suit their needs and can be used as separate dwelling with its own HVAC, bath & kitchen or perhaps rented out for income or simply used as a guest house. As you enter into the residence you will notice the 10 ft beamed ceilings, dark woodwork, stained glass and hardwood floors throughout. This property features two fireplaces, two jacuzzi tubs, two stairways and a 2nd floor rear balcony. The 1st floor features a huge kitchen/dining room combo, pocket doors, kitchen nook, bathroom, & spare room. Front of basement is finished and boast a family room, game room, two bedrooms etc. Rear has mechanicals with newer furnace & hot water heaters, laundry room and walkout to yard. Second floor has master bedroom & 3 additional bedrooms. Third floor has 1 bedroom & two rooms that share a large hall closet. Did I mention the shed and long driveway? Showings for qualified buyers will be by appointment only. Come & see this Jewel and make it your own or invest and resale at a profit. "AS IS"

1036 E Hyde Park Boulevard, Chicago

$1,300,000

6 Beds ⋅ 6 Baths ⋅ 12286341 MLS ⋅ CLOSED Status

SOUTH KENWOOD BEAUTY IN THE HEART OF THE HISTORICAL DISTRICT-this elegant, historical Greystone was designed by Architects Wilson and Marshall and built in 1896. The craftsmanship of its day is noticed from the exterior of the building, past the wrought iron fence and once you step inside. This elegant home features three levels of living above grade, 6 bedrooms and 5 1/2 baths has the bonus of a large three-bedroom coach house with 2 full bathrooms above the 3-car garage. Coach house is great for extended family stays or as added income. First floor has second staircase to the second floor. Other features are arched doorway, built-ins, tons of light. Coach house is so sweet and is large and homey. Home sits on 50' x 150' lot which allows for the side lot to be used to garden, read, party, play, relax, etc. With its high ceilings, original wood moldings, original inlaid rift-sawn oak floors, uniquely crafted staircase, fireplaces, stained glass windows, multiple ensuite bedrooms, and so much more. Full semi-finished high-high ceiling basement adds for more living space. Separate HVAC systems for house and coach house. Lake, university, museums, restaurants, and so much more. This masterful built home is awaiting your furniture. A REAL GEM!!!

4950 S Ellis Avenue, Chicago

$3,645,000

6 Beds ⋅ 7 Baths ⋅ 12216908 MLS ⋅ CLOSED Status

This magnificent residence is located on a verdant tree-lined street in the heart of the Kenwood Historic District. While constructed after the turn of the last century, the house has been elegantly and thoroughly updated for life in the current one. Horatio R. Wilson was a well-respected architect of his time, and his work is known for structural integrity and quality of materials - each of which are apparent decades after he first conceived of the design. Sited on a ridge that once ran across the Kenwood landscape, the impressive house had been meticulously maintained by former owners, and that stewardship continues. Behind the handsome facade of the nearly 8,000 square foot house is a wide array of aesthetic and mechanical improvements recently completed. The latest renovation (following an earlier gut rehab) included extensive masonry work, new windows, floors sanded and refinished, fireplaces relined and chimneys tuckpointed, new lighting, new bathrooms; all combine to make this a home that is a rarity in the neighborhood - truly move in ready. The quality of the residence is apparent the moment one enters the foyer, with an elegant carved stairway that rises the full three levels, capped by a dramatic skylight. The refined layout of the main level offers a formal living and dining rooms, a library (each with a fireplace) and a kitchen that was transformed by John Vinci, a living legend of Chicago architecture. The stunning space offers Bulthaup cabinetry, with vistas that extend to the lush exterior through a glass wall to covered porch framed by commercial grade railings and staircase, accented by recessed lighting in the warmth of a wood slat ceiling. The second and third levels of the house each feature three bedrooms and multiple baths, of which the Primary Bath is truly a room with a view. Large welcoming landings, hardwood floors, walk-in closets, vintage woodwork, crown moldings, leaded glass - the amenities are too numerous to list! And they continue on the lower level, with a mud room complete with dog spa, exercise room, additional full laundry, game room, family room and storage. The coach house was fully renovated and accommodates two cars (with EV charger) below the contemporary one-bedroom apartment. Kenwood is a short 8-minute drive from the Loop, near the University of Chicago, Laboratory Schools and all the Hyde Park community has to offer. A stunning property where you can with the next chapter of its extraordinary history.

4943 S Woodlawn Avenue, Chicago

$3,200,000

5 Beds ⋅ 6 Baths ⋅ 12071495 MLS ⋅ CLOSED Status

This absolutely fantastic home was meticulously and fully rehabbed by the current owners, and the result is a perfect combination of timeless elegance and comfortable modern living. Located on one of the most desirable blocks in the South Kenwood Historic landmark district, it retains many of the original's irreplaceable 19th century architectural features: high ceilings, oak hardwood floors throughout, large mostly south-facing windows allowing for an abundance of natural light, a majestic carved oak winding staircase past leaded-glass windows. At the same time there is woven in a seamless integration of a thoroughly modern aesthetic, from the open floor plan on the main level to the spacious and welcoming top floor primary suite of rooms. This one-of-a-kind home presents a stunning curb appeal, situated on an oversized lot professionally landscaped with mature plantings. The absolutely charming adjacent coach house contains a 3-car garage and an upstairs 2-bedroom, 1-bath apartment, currently rented.

4751 S Kimbark Avenue, Chicago

$1,495,000

8 Beds ⋅ 5 Baths ⋅ 12128447 MLS ⋅ CLOSED Status

Welcome to historic Kenwood, where yesterday's grandeur meets today's elegance. Nestled on a scenic double lot, this grand three-story home formerly known as The Duchisois Residence and designed by F.R. Schock is located in the South Kenwood Historical District. This stunning 8-bedroom, 5-bathroom home exudes vintage charm with its original oakwood floors, trim, solid core doors, and three original fireplaces. Offering nearly 6500 sq ft of luxurious living space, it features recessed lighting throughout, updated electric and plumbing, a new roof installed in 2014, a newly installed boiler, and separate central air systems. The grand foyer entry with parlor showcases gorgeous stained glass. The formal living and dining spaces and main level family room provide ample space for entertaining. The master bedroom suite includes a spa bath, while spacious bedrooms on the 2nd and 3rd floors offer comfort and style, including a large cedar closet. The modern gourmet kitchen boasts built-in custom appliances, and updated baths enhance the home's appeal. The lower recreational space has a wet bar and a second functional kitchen adding versatility. Outside, a huge detached 2-car garage with a 1000 sq ft coach house on top complements the incredible gated yard featuring a luxurious patio and mature landscaping. Walking distance to Lake Michigan, shopping, and museums. Easy to show with occupancy upon closing. This is a rare opportunity to own a piece of Kenwood history.

4800 S Kenwood Avenue, Chicago

$1,600,000

9 Beds ⋅ 6 Baths ⋅ 12100303 MLS ⋅ CLOSED Status

Welcome to a rare gem on one of historic Kenwood's most desirable tree-lined streets. The Alonzo Fuller House and Coach House, built in 1890, offer approximately 9,550 sq. ft., 8250 sq. ft. in the main house, and 1,300 sq. ft. in the coach house, all situated on a generous half-acre lot. This extraordinary property features three stories, an unfinished basement, and a four-car garage with a coach house. Step inside to discover a wealth of historic charm and character, including oak and parquet flooring, original trim and millwork, arched windows, turret rooms, coiffured ceilings, and magnificent original fireplaces. Designed by architect Federick W. Perkins, this expansive Queen Anne-style home welcomes you with a grand foyer and an exquisite staircase adorned with oak spindles and banisters. Entertain in style with a parlor, formal living room, and dining room featuring a bay window and a butler's pantry. The light-filled kitchen, with original maple floors and large windows, offers serene views of the picturesque backyard and coach house. The second floor features five spacious bedrooms with generous closets and two full bathrooms. The third floor offers the primary bedroom with an ensuite bath and walk-in closet, a versatile study/family room/ballroom with a fireplace, two additional bedrooms, a full bathroom, and the remnants of a convenient kitchenette, ideal for formal entertaining or everyday enjoyment.The unfinished basement presents endless possibilities, whether you envision a wine cellar with a tasting room, a hidden speakeasy, recreation room, full in-home gym, or game room. Outside, the property boasts a striking exterior of limestone and red brick, a driveway, a slate roof, and a heated four-car garage with storage, a workroom, and a coach house. The coach house includes two bedrooms, a bath, living and dining areas, and a sitting room, perfect for accommodating guests or multi-generational living. Experience Kenwood living in this exceptional residence. This magnificent home awaits your vision to carry it through the next several decades.

4832 S Ellis Avenue, Chicago

$455,000

7 Beds ⋅ 6 Baths ⋅ 12020593 MLS ⋅ CLOSED Status

**Captivating Investment Opportunity: 1880's Victorian & Brick Coach House** Welcome to a rare gem in the Kenwood/Hyde Park Community. Nestled on a sprawling 19,000+ square feet lot, this property presents an exceptional investment opportunity for savvy investors seeking prime real estate for development. **Property Highlights:** - **Historic Charm:** Built in the 1880s, the Victorian residence exudes timeless elegance, while the brick Coach House adds character and versatility to the property. - **Expansive Lot:** Spanning over 19,000 square feet, this sizable lot boasts a length of 284 feet, offering ample space for various development possibilities. - **Premier Location:** Situated in a coveted location, the property enjoys easy access to major amenities, renowned schools, and vibrant entertainment hubs, making it an ideal choice for prospective buyers. - **Alley Access:** With alley access on the entire east side and north end of the lot, developers have the convenience of easy ingress and egress for construction purposes, enhancing the appeal for potential projects. **Development Potential:** The generous lot size and strategic location make this property an excellent canvas for development projects such as: - **Row-Homes:** With the lot's dimensions, there's potential for the creation of row-homes, catering to the demand for upscale urban living. - **Condo Building:** Explore the possibility of constructing a modern condo building, offering luxury residences that capitalize on the area's desirability. - **Multi-Unit Development:** Utilize the vast space to develop a multi-unit residential complex, accommodating the growing demand for rental properties in the area. **Property Details:** - **Victorian Residence:** Offering approximately 5500 square feet of living space, the Victorian residence awaits restoration, presenting an opportunity to breathe new life into its historic charm. - **Brick Coach House:** Comprising approximately 3000 square feet, the Coach House provides additional space and potential for renovation or repurposing to suit your vision. **Renovation Opportunity:** While the Victorian and Coach House are in need of renovation, this presents a blank canvas for investors to reimagine and revitalize these structures, adding significant value to the property. **Don't Miss Out:** Rarely does an opportunity of this caliber present itself. Whether you're an experienced developer or an investor seeking to diversify your portfolio, this property offers endless potential and promises substantial returns on investment. Contact us today to schedule a viewing and unlock the possibilities that await with this remarkable real estate opportunity.

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Coach House Homes in Kenwood, Chicago IL

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